This invention relates to cationic unsaturated mono- and polysaccharide glycoside derivatives, as well as to the polymers derived therefrom.
Ethylenically unsaturated mono- and disaccharide glycoside derivatives as well as homo- and copolymers derived therefrom have been prepared. See, for example, U.S. Pat. No. 3,356,652 issued on Dec. 5, 1967 to D. Ray-Chaudhuri which describes the preparation of a glycoside containing an ethylenically unsaturated side-chain linked to the number 1 carbon of a 2,3,4,6-tetra-O-acetylglucose molecule by reacting a tetraacetylglycosyl halide with a monohydroxy or monocarboxy ethylenically unsaturated monomer. The homo- and copolymers prepared from the acetylated glycosidic monomers are soluble in organic solvents. Upon deacetylation, the homo- and copolymers having a mole fraction of at least 20% of the glucoside derivatives become readily water soluble with a greater hydrophilic character than other commonly available synthetic water soluble polymers. The polymers are described as having broad utility in the adhesive, textile, and paper industries.
Similarly, U.S. Pat. No. 4,328,337 issued May 4, 1982 to T. Kawasaki et al. describes the preparation of high polymeric substances having repeating mono- or disaccharide side chains prepared by homopolymerizing (meth)acroyl mono- or disaccharide glycosides. These high polymers are described as being water soluble with excellent bio-adaptability and having a membrane-forming property. When cross-linked, the homopolymers have a high water-retaining property which is useful for many medical treatments.
In U.S. Pat. No. 3,931,148 issued on Jan. 6, 1976 to W. Langdon, novel neutral and cationic glycosidic surfactants are prepared by reacting a 2-hydroxy-3-chloropropyl glycoside of a mono- or polysaccharide with an alkyl amine which contains at least one hydrophobic C.sub.8 -C.sub.18 alkyl group. The alkyl amines are described as having 8-30 carbon atoms which may be primary, secondary, tertiary, aliphatic, saturated or unsaturated, alicyclic and aralkyl. The glycosides are described as being useful in areas requiring surfactants exhibiting biodegradability, alkali solubility and stability.
Due to the low cost and abundance of many saccharides in addition to the hydrophilic nature they provide to polymers, it is the prime objective of this invention to produce a novel class of cationic unsaturated mono- and polysaccharide glycoside derivatives, the derivatives being capable of undergoing homopolymerization or copolymerization in the presence of other unsaturated comonomers. None of the above references disclose or suggest the products of the present invention.